HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Bromobutane → HCID 71295313, compound

HRID 527200
Notes
Print preview

Reaction equation

HRID 527200 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:22]2[C:26](=[O:27])[NH:25][N:24]=[CH:23]2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Br[CH:35]([CH2:37][CH3:38])[CH3:36]>CS(C)=O.O>[CH:35]([N:25]1[C:26](=[O:27])[N:22]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:9][CH2:10][N:11]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[CH2:12][CH2:13]3)=[C:2]([F:1])[CH:3]=2)[CH:23]=[N:24]1)([CH2:37][CH3:38])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 65542-BromobutaneHCID 11430Potassium CarbonateHCID 90310677HCID 90310677, compound

Product 1

HCID 71295313HCID 71295313, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Procedure

To a suspension of triazolone 7 (0.11 g, 0.3 mmol) in dimethylsulfoxide (4 mL) was added K2CO3 (0.08 g, 0.6 mmol). The resulting mixture was stirred at room temperature for 1 h. After the addition of 2-bromo butane (0.05 mL, 0.45 mmol), the temperature increased to 80° C. for overnight. After cooling to room temperature, the reaction mixture was diluted with water and extracted with dichlormethane. The combined organic layer was dried over Na2SO4, filtered, and concentrated to yield the crude product, which was purified by column chromatography to obtain triazolone 8 (0.11 g, 87%). 1H NMR (400 MHz, CDCl3, δH): 7.64 (s, 1H), 7.37 (dd, J=13.0, 2.2 Hz, 1H), 7.26-7.24 (m, 1H), 7.04 (t, J=8.8 Hz, 1H), 6.99-6.97 (m, 2H), 6.88-6.84 (m, 2H), 4.31-4.26 (m, 1H), 3.77 (s, 3H), 3.26 (bs, 8H), 1.86-1.81 (m, 1H), 1.73-1.71 (m, 1H), 1.38 (d, J=6.8 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H). 13C NMR (100 MHz, CDCl3, δC): 154.6, 154.2, 151.6, 139.4, 133.3, 128.4, 119.4, 118.7, 118.0, 114.5, 111.0, 110.8, 55.6, 52.8, 51.0, 50.5, 28.4, 19.3, 10.8.

Workup

  1. temperaturethe temperature increased to 80° C. for overnight
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with dichlormethane
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-38e6c9f071394e908ffe8bb10e0c5203
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346791B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes